PIBOSEROD

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H31N3O2
Molecular Weight	369.5004
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCN1CCC(CNC(=O)C2=C3OCCCN3C4=C2C=CC=C4)CC1

InChI

InChIKey=KVCSJPATKXABRQ-UHFFFAOYSA-N

InChI=1S/C22H31N3O2/c1-2-3-11-24-13-9-17(10-14-24)16-23-21(26)20-18-7-4-5-8-19(18)25-12-6-15-27-22(20)25/h4-5,7-8,17H,2-3,6,9-16H2,1H3,(H,23,26)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19567409 | https://clinicaltrials.gov/show/NCT00041496 | https://www.ncbi.nlm.nih.gov/pubmed/10571599

Piboserod (SB 207266) is a selective 5-HT(4) receptor, antagonist. The 5-HT4 receptor antagonists are thought to antagonize both the ability of serotonin to sensitize the peristaltic reflex and 5-HT-induced defecation, at least in animal studies. As 5-HT4 receptors are present in human atrial cells and when stimulated may cause atrial arrhythmias, piboserod was under investigation in clinical trials for atrial fibrillation. In addition, GlaxoSmithKline studied the drug for the management of irritable bowel syndrome. Nevertheless, development both indications had been discontinued. Piboserod has successfully passed phase II clinical trials for the treatment of patients with congestive heart failure.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
5-hydroxytryptamine receptor 4 8 Target ID: Q13639\|\|\|Q9NY73 Gene ID: 3360.0 Gene Symbol: HTR4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15902472	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Atrial fibrillation 131 Sources: https://clinicaltrials.gov/show/NCT00041496	Preventing	Phase II 1132	Unknown Approved Use Unknown
Heart failure 103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19567409	Primary	Phase II 1132	Unknown Approved Use Unknown
Irritable bowel syndrome 60 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10571599	Primary	Not Provided 504	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00AC1Y	https://www.1pchem.com/search?query=1P00AC1Y
AbovChem LLC	HY-15574A	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-15574A
AstaTech	FD10684	http://astatechinc.com/CPSResult.php?CRNO=FD10684
Axon MedChem	1098	https://www.axonmedchem.com/product/1098
BLD Pharm	BD147984	http://www.bldpharm.com/search/Search.html?keyword=BD147984
BLD Pharm	BD630459	http://www.bldpharm.com/search/Search.html?keyword=BD630459
BOC Sciences	152811-62-6	http://www.bocsci.com/description.asp?cas=152811-62-6
BOC Sciences	178273-87-5	http://www.bocsci.com/description.asp?cas=178273-87-5
Cayman Chemical	18778	http://www.caymanchem.com/app/template/Product.vm/catalog/18778
Chem Scene	CS-4311	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-4311
ChemShuttle	186239	https://www.chemshuttle.com/catalogsearch/result/?q=186239
Excenen	EX-A1189	http://www.excenen.com/searchresultlist.php?id=EX-A1189
Fluorochem	535788	http://www.fluorochem.co.uk/Products/Product?code=535788
Lab Network	LN01343230	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343230
MedChem Express	HY-15574	https://www.medchemexpress.com/search.html?q=HY-15574&ft=&fa=&fp=
MolPort	MolPort-005-942-597	https://www.molport.com/shop/molecule-link/MolPort-005-942-597
MolPort	MolPort-042-665-633	https://www.molport.com/shop/molecule-link/MolPort-042-665-633
Molnova	M17331	https://www.molnova.com/en/serch-list.html?keywords=M17331
MuseChem	I001904	https://www.musechem.com/product/I001904.html
MuseChem	I002311	https://www.musechem.com/product/I002311.html
Ryan Scientific	ITD-1	https://ryansci.com/products?q=ITD-1&list_q=&search_type=exact
ShangHai Biochempartner	BCP15982	http://www.biochempartner.com/search_BCP15982
TargetMol	T2278	https://www.targetmol.com/search?keyword=T2278
Toronto Research Chemicals	P431925	https://www.trc-canada.com/product-detail/?CatNum=P431925
eMolecules	300489704	https://orderbb.emolecules.com/search/#?query=300489704
eMolecules	36366900	https://orderbb.emolecules.com/search/#?query=36366900
eMolecules	64090148	https://orderbb.emolecules.com/search/#?query=64090148
eNovation Chemicals	D508434	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D508434&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-3471879348	https://mcule.com/MCULE-3471879348/
mcule	MCULE-8849995922	https://mcule.com/MCULE-8849995922/

PubMed

Title	Date	PubMed
Cloning and expression of human 5-HT4S receptors. Effect of receptor density on their coupling to adenylyl cyclase.	1997 Oct 20	9351641
Synthesis and pharmacological activity of metabolites of the 5-HT(4) receptor antagonist SB-207266.	2001 Aug	11504648
The 5-HT4 receptor agonist, tegaserod, is a potent 5-HT2B receptor antagonist in vitro and in vivo.	2004 Nov	15466450
Piboserod (SB 207266), a selective 5-HT4 receptor antagonist, reduces serotonin potentiation of neurally-mediated contractile responses of human detrusor muscle.	2005 Jun	15902472
Measurement of 5-HT4 receptor-mediated esophageal responses by digital sonomicrometry in the anesthetized rat.	2006 May-Jun	16168678

Patents

Sample Use Guides

In Vivo Use Guide

Piboserod 80 mg for 24 weeks including 4 weeks up titration.

Route of Administration: Oral

In Vitro Use Guide

The pharmacology of piboserod (SB 207266) has been evaluated in vitro in the guinea-pig distal colon longitudinal muscle myenteric plexus (LMMP). SB 207266 is a highly potent antagonist of 5-HT-evoked, cholinergically-mediated contractions in the guinea-pig distal colon. Low concentrations (0.1-10 nM) produced a parallel shift to the right of the concentration-effect curve (apparent pA2 10.6 +/- 0.1) with no significant effect on the maximum response. With higher concentrations of SB 207266 (30 nM and above) the maximum response to 5-HT was reduced. SB 207266 is not an irreversible antagonist since the effects of the compound were reversible upon washing of the tissue.

Name

Type

Language

PIBOSEROD

Official Name

English

piboserod [INN]

Common Name

English

N-((1-BUTYL-4-PIPERIDYL)METHYL)-3,4-DIHYDRO-2H-(1,3)OXAZINO(3,2-A)INDOLE-10-CARBOXAMIDE

Systematic Name

English

2H-(1,3)OXAZINO(3,2-A)INDOLE-10-CARBOXAMIDE, N-((1-BUTYL-4-PIPERIDINYL)METHYL)-3,4-DIHYDRO-

Systematic Name

English

Piboserod [WHO-DD]

Common Name

English

PIBOSEROD [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885